Have you thought about an exit strategy from tech?

I can chime in here having grown up in Silicon Valley, and my dad is literally a software engineer as well who retired around 60 who knows a bunch of other software engineers who are 50+.

It seems like there aren’t a ton of older engineers (say, past their 50's) in hands-on SWE roles...

This is actually not the case from what I've seen. The reason you might perceive this is because older folks tend to work at companies that young people tend to avoid. Also, there are simply far more young software engineers than older software engineers as the tech boom really started in the early 2010s with the rise of FAANG. Before, we didn't have $1 trillion market cap companies and the dot-com bust also forced many older software engineers to leave the entire industry (many younger folks don't understand how bad 2000 was).

I’d love to hear if anyone has seen or heard of successful transitions out of tech.

For the Bay Area in particular, a very common exit is to go into real estate. I know so many engineers like my dad who bought Bay Area homes after the 2008 recession and are now just property managers for a living.

Unfortunately, I don't think this can be really replicated now as Bay Area homes are stupidly expensive due to the software boom starting in the early 2010s and limited housing supply.

Keep in mind, as a field, software engineering is a young field. The number of engineers now is way higher than 30-40 years ago (the cohort of tech people who would be retiring now). So there are limited data points.

Another confounding variable is that anyone who joined a fast-growing startup (or generally any tech co) 20-30 years ago likely has plenty of money now 💸💸

So they may have left tech simply because they hit their financial goals, and they're not gardening, traveling, or just doing family stuff.

As someone who's both thought about and implemented it :), I have this to say:

• What keeps most people from actually exiting is the prospect of losing their (big) paychecks since very few professions pay as much as tech. So the process is as much inner work and mental preparation as it is tactically identifying what to do next.
• The next hurdle is the saturated gig economy. Pre-pandemic, more than one generation never questioned why we work so much. But pandemic forced everyone to slow down and many people realized the freedom in being their own boss and setting their own schedule.
  • But to actually do it, you have to spend a lot of time on networking, marketing, and sales for your venture, which many hate.
  • So, again, the actual work lies in preparing yourself to play these roles and learn their ropes.
  • Being very good at your chosen profession is also important to have a differentiator and beat competition.
• The last step of course is to identify what to actually do. For me, I followed the aspect of my job that I felt passionate about and gave me the most satisfaction—mentoring engineers effectively as that was not happening for most people.
  • Once you're OK with the first two points, looking within is what I recommend to identify your next career.

I hope this helps.